Book Holiday Homes in Cutler

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

Featured Holiday Homes in Cutler

Gardner Lake Home:  Amazing views private and quiet  150' of private frontage

Gardner Lake Home: Amazing views private and quiet 150' of private frontage

East Machias
When you stay at this vacation home in East Machias, you'll be 14 minutes by car from Bad Little Falls Park.
Gardner Lake Home: Amazing views private and quiet 150' of private frontage
Beautiful Downeast Maine Family Lakeside Rental!

Beautiful Downeast Maine Family Lakeside Rental!

East Machias
When you stay at this vacation home in East Machias, you'll be on a lake and 15 minutes by car from Bad Little Falls Park.
Beautiful Downeast Maine Family Lakeside Rental!
Oceanfront Home; A Coastal Maine Woodland Retreat

Oceanfront Home; A Coastal Maine Woodland Retreat

Cutler
When you stay at this vacation home in Cutler, you'll be on the waterfront and 11 minutes by car from The Bold Coast.
Oceanfront Home; A Coastal Maine Woodland Retreat
Save an average of 15% on thousands of hotels when you're signed in
WOW! Amazing property with an amazing view.  You will never want to leave!

WOW! Amazing property with an amazing view. You will never want to leave!

Jonesport
With a stay at this vacation home in Jonesport, you'll be by the ocean, and 19.5 mi (31.3 km) from Roque Bluffs State Park and 20.2 mi (32.4 km) from Bad Little ...
WOW! Amazing property with an amazing view. You will never want to leave!
Elegant log home with unobstructed ocean views

Elegant log home with unobstructed ocean views

Cutler
When you stay at this vacation home in Cutler, you'll be on the beach and 13 minutes by car from The Bold Coast.
Elegant log home with unobstructed ocean views
Serene Jonesport Escape: Deck w/ Water Views!

Serene Jonesport Escape: Deck w/ Water Views!

Jonesport
With a stay at this vacation home in Jonesport, you'll be on the waterfront, and 16.5 mi (26.5 km) from Roque Bluffs State Park and 17.2 mi (27.7 km) from Bad ...
Serene Jonesport Escape: Deck w/ Water Views!
Portside on Holmes Bay with ever-changing panoramic vistas of the Bold Coast.

Portside on Holmes Bay with ever-changing panoramic vistas of the Bold Coast.

Machiasport
Located in Machiasport, this vacation home is by the sea, within a 15-minute drive of Bad Little Falls Park and The Bold Coast.
Portside on Holmes Bay with ever-changing panoramic vistas of the Bold Coast.
Come enjoy oceanview in a lobsterfishing community at our  Moosabec Reach home.

Come enjoy oceanview in a lobsterfishing community at our Moosabec Reach home.

Jonesport
With a stay at this vacation home in Jonesport, you'll be on the waterfront, and 20.5 mi (32.9 km) from Roque Bluffs State Park and 21.2 mi (34 km) from Bad ...
Come enjoy oceanview in a lobsterfishing community at our Moosabec Reach home.
Cottage on Sawyer’s Cove

Cottage on Sawyer’s Cove

Jonesport
With a stay at this vacation home in Jonesport, you'll be on the waterfront, and 19.2 mi (31 km) from Roque Bluffs State Park and 19.9 mi (32.1 km) from Bad ...
Cottage on Sawyer’s Cove
Don't see what you're looking for?
See all available properties in Cutler
View all properties
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Cutler Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Cutler vacation homes are the perfect way for you to wing it.

Holiday houses in Cutler let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Cutler in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Cutler adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Cutler with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Cutler vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Cutler Holiday Homes essential information

Accommodation
80 Holiday Homes
Lowest Price
Highest Price
Popular accommodation
Gardner Lake Home: Amazing views private and quiet 150' of private frontage, Beautiful Downeast Maine Family Lakeside Rental!, Oceanfront Home; A Coastal Maine Woodland Retreat, WOW! Amazing property with an amazing view. You will never want to leave! , Elegant log home with unobstructed ocean views, Serene Jonesport Escape: Deck w/ Water Views!, Portside on Holmes Bay with ever-changing panoramic vistas of the Bold Coast., Come enjoy oceanview in a lobsterfishing community at our Moosabec Reach home., Cottage on Sawyer’s Cove

Top trending hotels in Cutler

Oceanfront Home; A Coastal Maine Woodland Retreat

Oceanfront Home; A Coastal Maine Woodland Retreat

Cutler
When you stay at this vacation home in Cutler, you'll be on the waterfront and 11 minutes by car from The Bold Coast.
Oceanfront Home; A Coastal Maine Woodland Retreat
Bear Beach Maine! Oceanfront Log Cabin, Secluded Sandy Beach, Sunsets & Sauna

Bear Beach Maine! Oceanfront Log Cabin, Secluded Sandy Beach, Sunsets & Sauna

Cutler
When you stay at this cabin in Cutler, you'll be on the beach and 14 minutes by car from The Bold Coast.
Bear Beach Maine! Oceanfront Log Cabin, Secluded Sandy Beach, Sunsets & Sauna
Elegant log home with unobstructed ocean views

Elegant log home with unobstructed ocean views

Cutler
When you stay at this vacation home in Cutler, you'll be on the beach and 13 minutes by car from The Bold Coast.
Elegant log home with unobstructed ocean views
Save an average of 15% on thousands of hotels when you're signed in
Harbor View Cottage Maine, 150+ years old

Harbor View Cottage Maine, 150+ years old

Cutler
Located in Cutler, this vacation home is by the ocean, a 4-minute drive from The Bold Coast and 6 minutes from Cutler Coast Public Reserved Land.
Harbor View Cottage Maine, 150+ years old
Don't see what you're looking for?
See all available properties in Cutler
View all properties
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.